Triethylamine → HCID 1120195, 화합물

HRID 1818074노트

반응식

HRID 1818074 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:16][NH2:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=[C:26]1[C:34](Cl)=[O:35]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:16][NH:17][C:34]([C:26]3[O:25][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[CH:27]=3)=[O:35])[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 739193STK362959

생성물 1

HCID 1120195HCID 1120195, 화합물수율 78%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

C-[1-(3,4-Dimethoxy-phenyl)-cyclopentyl]-methylamine (141 mg, 0.600 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL) containing triethylamine (167 μL, 1.20 mmol). Benzofuran -2-carbonyl chloride (108 mg, 0.600 mmol) was then added and the reaction mixture was allowed to stir for 16 hours. The reaction mixture was filtered, evaporated to dryness, and purified by column chromatography on silica gel using a gradient of 5-50% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (0.1775 g, 0.4678 mmol, 78.0%) ESI-MS m/z calc. 379.5, found 380.2 (M+1)+. Retention time of 3.36 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.57-2.03 (m, 8H), 3.46 (d, J=6.4 Hz, 2H), 3.72 (s, 6H), 6.81-6.89 (m, 3H), 7.31 (t, J=7.5 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 7.48 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.94 (t, J=6.3 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ 23.1, 35.3, 47.2, 51.8, 55.5, 109.2, 111.5, 111.6, 111.7, 118.8, 122.6, 123.6, 126.7, 127.1, 139.3, 147.1, 148.3, 149.1, 154.1, 158.2.

후처리

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. custompurified by column chromatography on silica gel using a gradient of 5-50% ethyl acetate in hexanes
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-1059de7be54140e3a6d2c7cb49b67dc2
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598412B2

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